Synthesis and characterization of novel (oligo)thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications

Rosa M. F. Batista; Susana P. G. Costa; M. Belsley; Carlos Lodeiro; M. Manuela M. Raposo

doi:10.1016/j.tet.2008.07.043

Synthesis and characterization of novel (oligo)thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications

Rosa M. F. Batista, Susana P. G. Costa, M. Belsley, Carlos Lodeiro, M. Manuela M. Raposo

Research output: Contribution to journal › Article › peer-review

81 Citations (Scopus)

Abstract

A series of new heterocyclic chromophores 3-6 were synthesized in moderate to excellent yields by condensation of 5,6-phenantroline-dione with formyl-thiophene derivatives 1-2 in the presence of ammonium acetate in glacial acetic acid. These chromophores possess an (oligo)thienyl π-conjugated system attached to an imidazo-phenanthroline moiety. These derivatives were evaluated concerning their solvatochromic properties, thermal stabilities, and molecular optical nonlinearities.

Original language	English
Pages (from-to)	9230-9238
Number of pages	9
Journal	Tetrahedron
Volume	64
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2008.07.043
Publication status	Published - 22 Sep 2008

Keywords

π-Conjugated systems
Hyper-Rayleigh scattering (HRS)
Imidazole
Nonlinear optics (NLO)
Phenanthroline
Solvatochromic probes
Thermal stability
Thiophene

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@article{735d15e91edf4c7f8981d2015557a2ab,

title = "Synthesis and characterization of novel (oligo)thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications",

abstract = "A series of new heterocyclic chromophores 3-6 were synthesized in moderate to excellent yields by condensation of 5,6-phenantroline-dione with formyl-thiophene derivatives 1-2 in the presence of ammonium acetate in glacial acetic acid. These chromophores possess an (oligo)thienyl π-conjugated system attached to an imidazo-phenanthroline moiety. These derivatives were evaluated concerning their solvatochromic properties, thermal stabilities, and molecular optical nonlinearities.",

keywords = "π-Conjugated systems, Hyper-Rayleigh scattering (HRS), Imidazole, Nonlinear optics (NLO), Phenanthroline, Solvatochromic probes, Thermal stability, Thiophene",

author = "Batista, {Rosa M. F.} and Costa, {Susana P. G.} and M. Belsley and Carlos Lodeiro and Raposo, {M. Manuela M.}",

note = "Thanks are due to the Fundacao para a Ciencia e Tecnologia (Portugal) for financial support through Centro de Quimica - Universidade do Minho (project PTDC/QUI/66250/2006, PhD grant to R.M.F. Batista SFRH/BD/36396/2007) and Departamento de Fisica (Universidade do Minho) and Departamento de Quimica (FCT-UNL) RFQUIMTE.",

year = "2008",

month = sep,

day = "22",

doi = "10.1016/j.tet.2008.07.043",

language = "English",

volume = "64",

pages = "9230--9238",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "39",

}

Synthesis and characterization of novel (oligo)thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications. / Batista, Rosa M. F.; Costa, Susana P. G.; Belsley, M.; Lodeiro, Carlos; Raposo, M. Manuela M.

In: Tetrahedron, Vol. 64, No. 39, 22.09.2008, p. 9230-9238.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and characterization of novel (oligo)thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications

AU - Batista, Rosa M. F.

AU - Costa, Susana P. G.

AU - Belsley, M.

AU - Lodeiro, Carlos

AU - Raposo, M. Manuela M.

N1 - Thanks are due to the Fundacao para a Ciencia e Tecnologia (Portugal) for financial support through Centro de Quimica - Universidade do Minho (project PTDC/QUI/66250/2006, PhD grant to R.M.F. Batista SFRH/BD/36396/2007) and Departamento de Fisica (Universidade do Minho) and Departamento de Quimica (FCT-UNL) RFQUIMTE.

PY - 2008/9/22

Y1 - 2008/9/22

N2 - A series of new heterocyclic chromophores 3-6 were synthesized in moderate to excellent yields by condensation of 5,6-phenantroline-dione with formyl-thiophene derivatives 1-2 in the presence of ammonium acetate in glacial acetic acid. These chromophores possess an (oligo)thienyl π-conjugated system attached to an imidazo-phenanthroline moiety. These derivatives were evaluated concerning their solvatochromic properties, thermal stabilities, and molecular optical nonlinearities.

AB - A series of new heterocyclic chromophores 3-6 were synthesized in moderate to excellent yields by condensation of 5,6-phenantroline-dione with formyl-thiophene derivatives 1-2 in the presence of ammonium acetate in glacial acetic acid. These chromophores possess an (oligo)thienyl π-conjugated system attached to an imidazo-phenanthroline moiety. These derivatives were evaluated concerning their solvatochromic properties, thermal stabilities, and molecular optical nonlinearities.

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KW - Hyper-Rayleigh scattering (HRS)

KW - Imidazole

KW - Nonlinear optics (NLO)

KW - Phenanthroline

KW - Solvatochromic probes

KW - Thermal stability

KW - Thiophene

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M3 - Article

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JO - Tetrahedron

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